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5 Days Exploring Chicago Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your day with a visit to the iconic Millennium Park, where you can see the famous Cloud Gate sculpture. Enjoy breakfast at Lou Malnati's Pizzeria, known for its deep-dish pizza.
Afternoon
Head over to the Art Institute of Chicago to explore its vast collection of art. For lunch, try the delicious offerings at Portillo's Hot Dogs, a local favorite.
Evening
End your day with a stroll along the Chicago Riverwalk, taking in the beautiful cityscape. Have dinner at Girl & The Goat, one of Chicago's most celebrated restaurants.
Bedtime
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4.69Millennium Park
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4.69Millennium Park
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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Cultural and Historical Highlights
Morning
Begin your day with a visit to the historic Field Museum. Afterward, enjoy breakfast at The Purple Pig, known for its inventive small plates.
Afternoon
Spend your afternoon exploring the fascinating exhibits at the Museum of Science and Industry. For lunch, head to Al's Beef for an authentic Italian beef sandwich.
Evening
Catch a show at the legendary Chicago Theatre and then dine at Au Cheval, famous for its burgers.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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Architectural Wonders and Sports
Morning
Visit the stunning architecture of the Rookery Building and enjoy breakfast nearby at The Publican.
Afternoon
Take a tour of the iconic Wrigley Field, home of the Chicago Cubs. Have lunch at Giordano's for another taste of deep-dish pizza.
Evening
Enjoy an evening concert or event at the famous United Center. Dine afterward at Joe's Seafood, Prime Steak & Stone Crab.
Bedtime
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4.73Rookery Building
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4.73Rookery Building
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4.86Wrigley Field
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4.86Wrigley Field
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Parks and Planetarium Day
Morning
Start your day with a relaxing walk through Grant Park. Have breakfast at nearby Frontera Grill, known for its Mexican cuisine.
Afternoon
Visit the fascinating exhibits at the Adler Planetarium. For lunch, stop by Pequod's Pizza for their renowned caramelized crust pizza.
Evening
Spend your evening exploring Navy Pier and enjoy dinner with a view at 360 Chicago Observation Deck (Formerly John Hancock Observatory)
Bedtime
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4.70Grant Park
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4.70Grant Park
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4.61Adler Planetarium
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4.61Adler Planetarium
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Final Day in Chicago
Morning
Begin your last day with a visit to Skydeck Chicago (Willis Tower) for breathtaking views. Enjoy breakfast nearby at Bavette’s Bar & Boeuf.
Afternoon
Explore Lincoln Park & Zoo before having lunch in Maple & Ash.
Evening
Conclude your trip with dinner in Alinea followed by live music in House of Blues.
Bedtime
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